(S)-1-bromo-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methoxymethoxy-2-butanone | 1448639-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-bromo-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methoxymethoxy-2-butanone
• 英文别名: (4S)-1-bromo-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(methoxymethoxy)butan-2-one
• CAS: 1448639-78-8
• 化学式: C₁₁H₁₉BrO₅
• 分子量: 311.173
• InChiKey: VHDXHTDTXGLSRW-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-bromo-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methoxymethoxy-2-butanone 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.91h， 生成 acortatarin A 、 xylapyrroside B
  参考文献：
  名称：

  Concise Total Synthesis of Acortatarin A

  摘要：

  The spirocyclic pyrrole alkaloid, acortatarin A, which had been isolated from a Chinese medicinal plant, was synthesized from a known olefinic compound by a concise six-step sequence involving N-alkylation of a pyrrole derivative with an a-bromo ketone intermediate as the key step.

  DOI：

  10.1271/bbb.120862
• 作为产物：
  描述：

  (R)-4-[(S)-1-methoxymethoxy-3-butenyl]-2,2-dimethyl-1,3-dioxolane 在 N-溴代丁二酰亚胺(NBS) 、 copper(II) acetate monohydrate 、 氧气 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.33h， 生成 (S)-1-bromo-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methoxymethoxy-2-butanone
  参考文献：
  名称：

  Concise Total Synthesis of Acortatarin A

  摘要：

  The spirocyclic pyrrole alkaloid, acortatarin A, which had been isolated from a Chinese medicinal plant, was synthesized from a known olefinic compound by a concise six-step sequence involving N-alkylation of a pyrrole derivative with an a-bromo ketone intermediate as the key step.

  DOI：

  10.1271/bbb.120862

文献信息

• Concise Total Synthesis of Acortatarin A
  作者：Takaaki TERANISHI、Masayuki KAGEYAMA、Shigefumi KUWAHARA

  DOI：10.1271/bbb.120862

  日期：2013.3.23

  The spirocyclic pyrrole alkaloid, acortatarin A, which had been isolated from a Chinese medicinal plant, was synthesized from a known olefinic compound by a concise six-step sequence involving N-alkylation of a pyrrole derivative with an a-bromo ketone intermediate as the key step.